Denatured alcohol containing a primary amine and chloroform



val VII Patented Sept. 3, 1940 DENATURED ALCOHOL CONTAINING A PRHVIARY AMINE AND CHLOROFORM Louis J. Figg, Jr., Kingsport, Tenn, assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application October 23, 1937, Serial No. 170,660

frightful odor of the isonitrile and the resulting practical certainty of detection would cause the bootlegger to discontinue his operations.

I prefer to use about equal parts, by volume, of chloroform and amine. From 0.5 to 5 parts of the mixture, per 100 parts of 95% alcohol, is sufficient for denaturing, although more maybe used if desired.

What I claim as my invention and desire to be secured by Letters Patent of the United States is:

7 Claims.

This invention relates to the denaturing of ethyl alcohol and to alcohol so denatured.

It is an object of my invention to provide a denaturant which will render ethyl alcohol containing it unfit for use as a beverage, which cannot be economically removed from the alcohol by any known methods, which will not render the alcohol unfit for industrial uses in which denatured alcohol has customarily been employed, and which will be free from methanol. It is a further object of my invention to provide 1. Denatured ethyl alcohol containing, as denatured alcohol which, when an attempt is essential denaturing elements, chloroform and a made to free it from its denaturants, becomes primary aliphaticlaminefiof from 3 to 8 .carbon even more unpotable. Other objects will hereatoms, whereby an isonitrile is formed when the inafter appear. denatured alcohol is heated with caustic alkali. I have discovered that a mixture of chloroform 2. Denatured ethyl alcohol containing, as and a primary aliphatic amine containing from essential denaturing elements, chloroform and a 3 to 8 carbon atoms is a particularly effective monopropylamine, whereby an isonitrile is denaturant. The mixture of amine and chloroformed when the denatured alcohol is heated form is colorless, has a pleasant odor, and imwith caustic alkali.

parts a disagreeable taste to ethyl alcohol. The- 3. Denatured ethyl alcohol containing, as amine inhibits any corrosion which might take essential denaturing elements, chloroform and a. place due to hydrolysis of the chloroform. monobutylamine, whereby an isonitrile isformed Now when a bootlegger attempts to clean when the denatured alcohol is heated with causdenatured alcohol, he almost invariably uses a tic alkali.

4. Denatured ethyl alcohol containing, as an essential denaturing element, from 0.5 to 5 parts, approximately, per 100 parts of 95% alcohol, of a mixture, in approximately equal proportions, of chloroform and a primary aliphatic amine of from 3 to 8 carbon atoms, whereby an isonitrile is formed when the denatured alcohol is heated with caustic alkali.

5. Denatured ethyl alcohol containing, as an essential denaturing element, from 0.5 to 5 parts, approximately, per 100 parts of 95% alcohol, of a mixture in approximately equal proportions of chloroform and a monopropylamine, whereby an isonitrile is formed when the denatured alcohol is heated with caustic alkali.

6. Denatured ethyl alcohol containing, as an essential denaturing element, from 0:5 to 5 parts, approximately, per 100 parts of 95% alcohol, of a mixture in approximately equal proportions of strong alkali such as sodium hydroxide. The usual procedure is to add the strong alkali to the still pot which contains the denatured alcohol, apply heat and distill. If the alcohol con- 3 tains chloroform and a primary amine, when it is heated with a strong alkali the carbylamine reaction takes place, with the formation of an isonitrile with an unbearable, putrid odor. The isonitriles are soluble in alcohol, so that the un- 35 bearable odor persists in the alcohol after heating is discontinued. Thus the removal of the denaturants is rendered impracticable, and the alcohol is rendered absolutely unpotable.

Methylamine and ethylamine are too volatile to remain in the alcohol, so that they cannot be effectively used in the practice of my invention. However, the primary aliphatic amines containing from 3 to 8 carbon atoms, such as propylamine, butylamine, amylamine, hexylamine, hep-.

45 tylamine, and octylamine, can be used'in carrying chloroform and a monobutylamine, whereby an out my invention. I prefer to use propylamine isonitrile is formed when the denatured alcohol or butylamine, because the boiling points of the is heated with caustic alkali. corresponding isonitriles are such that the 150- 7. Ethyl alcohol containing as a denaturant nitriles cannot be removed from the alcohol by a small quantity of a mixture in about equal 50 fractional distillation, no matter how hardy or molar proportions of a primary alkyl amine and ingenious the bootlegger might be, or how isochloroform. lated his still. Ordinarily, however, higher-boiling amines would also be effective, because the LOUIS J. FIGG, JR.

Patent No. 2,215,760.

CERTIFICATE OF CORRECTION.

1 September 5, '19140.

LOUIS J. FIGG, J'R. v

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, first column, line 50, after the word "primary" insert aliphatic; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 29th day of October, A. D. 19)+O..

Henry Van Arsdale,

(Seal) 7 v I Acting Commissioner of Patents.

CERTIFICATE OF CORRECTION.

Patent No. 2,215,760. September 5, 192 0.

LOUIS J. FIGG, JR.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follovire: Page 1, first column, line 50, after the word "primary" insert aliphaticand that the said hetters Patent should be read with this correction therein that the sen 1e may conform to the record of the case in the Patent Office.

Signed and sealed this 29th day of October, A..,D.' 191w.

Henry Van Arsdale,

(Seal) Acting Comis'sioner of Patents. I 

